


Betting Man's Game

by BewareTheIdes15



Category: Supernatural
Genre: Bets, Crossdressing, Lingerie, M/M, Sibling Incest, Wincest - Freeform
Language: English
Status: Completed
Published: 2011-07-04
Updated: 2011-07-04
Packaged: 2017-10-21 00:19:41
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,329
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/218721
Author URL: https://archiveofourown.org/users/BewareTheIdes15/pseuds/BewareTheIdes15
Summary: <blockquote class="userstuff">
              <p>Dean loses a bet and has to wear women's underwear for the day. Turns out that's kinda hot.</p>
            </blockquote>





	Betting Man's Game

Dean stomped out of the bathroom because stomping was manly even if you did have a red satin torture device on. Sam was standing by the door waiting on him with this shit-eating grin that was just begging to be punched.

"Let's go," Dean growled, feeling a little bit better about the situation with his leather jacket firmly in place. It still seemed like everybody was going to see through his clothes and just KNOW, like there was some kind of neon sign flashing over his head - 'Dean wears panties'.

They had always made bets with each other, their competitive natures combined with a crippling need to pass the time. From pool and darts to shooting practice to whether more red cars would pass them on the road than blue ones, they had always made stupid little wagers and the stakes had gotten them into trouble more than once. Dad had finally put a stop to it was Sam was 16 and had gotten arrested for running naked through town square to pay up on one of the bets and they hadn't ever picked back up with it. Until recently.

Dean probably should have known better than to trust it when Sam was game for betting on who could get the most girls numbers in the bar last night. Still, there had been some pretty healthy servings of bourbon before that, so Dean figured it wasn't entirely his fault that he hadn't noticed Sam - sneaky little shit - whispering quietly to all the women he passed. Apparently the idea of Dean in women's underwear had a universal appeal which had landed Sam a two-inch stack of cocktail napkin numbers. Dean wanted to die.

Of course, he really hadn't expected Sammy to rush out this morning before he was even awake and buy a damn thong, but it had been waiting for him when he woke up, wrapped neatly around his paper coffee cup. Had he mentioned he wanted to die?

Now the fucking thing was trying to climb inside him and hunting was going to be a fucking bitch like this so he hoped Sam was happy. Which certainly did appear to be the case from the way his little brother's grin just kept growing. Maybe if he waited long enough that giant smug face would just split in two.

Sam wagged a halting finger at him as Dean made for the door.

"What, dude?" he snapped in reply.

"Let's see 'em." A challenge sparked in Sam's hazel eyes and there wasn't anything in the bet about not punching him...

"What, you don't trust me?" he stalled. It was bad enough he had to wear the fucking thing, he didn't need to go flashing it around too. Besides, he wasn't the kid of guy to welch on a bet and Sammy should damn well know it.

"Not as far as I can throw you," Sam smiled, "Now show me that whale-tail, sweetheart."

One of them was definitely going to walk out of this with a black eye.

Dean grumbled, blood running hot - from anger, not embarrassment, Dean Winchester, mighty hunter, did not get embarrassed - and quickly flipped up his jacket and shirt, tugging down the waistband of his jeans to expose a line of red satin beneath. Sam was apparently at least smart enough to not make some stupid-ass comment that was going to force Dean to murder him, and just nodded his approval. Like Dean needed it.

He flung open the motel door and was halfway to the Impala before he heard Sam snicker,

"Pretty, pretty princess."

His shoulder crashed into his brother's midsection, toppling them both halfway back into the room, legs stuck out across the sidewalk. They were fighting between a couple of really effective wrestling holds - damn Sam's stupid, long arms - when they both froze at an 'ahem' close by.

A scandalized-looking woman was standing just to the side of their tangled legs, covering her little girl's eyes. She gave them both a dirty look and Dean was just in no kind of mood to take that shit from a stranger. He met her glare for glare and cocked his head to run his tongue slowly over the seam of Sam's lips. And that might have actually been better than beating him in a fight because Sam just straight up stopped breathing. Dean gave the woman one last little 'fuck you' wave as she rushed her daughter away and then began disentangling himself from his baby brother.

Sam was still laying on the dirty carpet, staring numbly at him. Now it was Dean's turn to smirk.

"Who's the princess now?"

***

They tumbled back into the room at close to two in the morning, tired and covered in grey muck from the knee down - fucking swamp monsters - but no worse for wear. Sam immediately began stripping out of his soiled jeans - they were really going to need to find a laundromat - since the bastard had claimed first shower.

Dean followed suit because, seriously, gross, and debated whether or not to just put on a fresh pair and go hit the bar again. He was tired, true, but a good hunt always left him with a certain kind of itch that he really needed another warm body to scratch. He wasn't all that dirty, maybe he'd change his shirt too and then -

"Dude, my eyes!" Sam shouted and for a second panic set in - did swamp monsters have some kind of sight-stealing venom he didn't know about? - before Dean realized that his little brother was giving him shit over the damn panties. Sam was standing there in nothing but his boxers, grimacing and holding his hands out in front of him like Dean was giving off blinding light.

"What? You were all eager to see them this morning," he taunted, turning in a little circle to give Sam the full view. He was actually kind of getting to like these things, not that he'd ever tell his brother that. They were soft and smooth and kind of cradled everything nicely. He could do with a little more room for his balls, but still.

"You know your butt is showing, right," Sam shot back playfully, "I mean, not the one on the front of your head, but like your real-"

Sammy managed to get out the way before Dean could tackle him this time, but the older brother was quicker and grabbed at one of Sam's legs, sending him falling onto the bed. Dean was on top of him in a second and after a couple of minutes of half-serious tussling, managed to get him pinned.

Dean had Sam's hands trapped over his head with one of his own and he sat back across Sam's hips. It wasn't lost on him that Sam was half-hard under the curve of his ass, but between the adrenaline from the hunt and their little scuffle, he was straining a little against the thong himself so he didn't see any reason to make a big deal out of it.

"What's wrong Sammy? You don't like them? Think I'd look better in blue?" he smirked and Sam's whole face went red.

"Get off me, assface," Sam retorted, struggling halfheartedly. Dean just leaned in smugly and sank his teeth into the smooth curve of Sam's peck, hard.

Well then. Hello. Apparently Sammy liked to be bitten. Like a lot. Well wasn't that interesting.

Dean sat back with a low chuckle and yeah, Sam's face was even redder than before. Dean gave a little wiggle with his hips to prove that he was definitely feeling what his baby brother was packing and Sam groaned miserably as his hips bucked up of their own accord.

"Dean, get off," he whined, carefully studying the lamp beside the bed.

"I know you think I'm easy Sammy, but it usually takes a little more than that. I need a little friction at least," he joked, not moving an inch.

"Ha fucking ha," Sam's eyes rolled.

It probably should have been weird with his little brother's big hard on pressing into his ass, but hell, they'd spent practically their whole lives in the same room together; the boundaries were kind of worn thin, only there for show nowadays anyway. Dean's body was giving the big thumbs up to being on top of Sammy and if there was one thing Dean had learned in his years of hunting, it was that his body was a lot smarter than his brain most of the time.

With that in mind, Dean shifted a little more weight onto the hand holding Sam's wrists, slowly rolling his hips. Sam sucked in a harsh breath and clenched his eyes tight.

"Dean-"

"Shh."

Another quick shift-move of his hips and the plummy head of Sam's cock was peeking out of the opening in his boxers. Dean rolled his satin-clad dick over it and Sammy's back arched in a perfect bowstring of pleasure.

"You like that, huh?" he purred, watching want and hesitation war on Sam's face, "Good choice with the satin, Sammy. Always knew you were a classy guy."

Sam's hips were slowly rocking against Dean's like they were moving against Sam's will. Dean matched the pace, letting his head roll back as the move sent waves of heat cascading up his spine.

"Fuck yeah," he breathed to the ceiling, Sam's hard length massaging his balls until he really needed to pound into something hard. Somebody. Somebody like Sammy.

Dean leaned in close again, chest meeting Sam's in a smooth line. The motion aligned their dicks, Dean's working its way past the waistband of the thong to rub against the silky heat of Sam's length. They both moaned in pleasure, Sammy's hips starting to work harder.

Dean's lips skated over the exposed skin of Sam's neck, tickling the flesh with feather-light caresses and breathing deep the scent of his brother. He licked softly at the warm skin and Sam made a choked noise in the back of his throat that Dean suspected was going to be a whimper. His chest tightened up with heat at the sudden need to hear that sound split the air so he switched from tongue back to teeth and bit savagely at tender flesh.

Sam bucked up hard underneath him and if Dean hadn't been laying flat over him he probably would have been thrown. The slide of their crowns against each other went slick and Dean's mouth flooded at the idea of tasting the sweet precome Sam was spreading over him. He sucked on the flesh between his teeth, bringing blood to the surface for a sharp purple bruise that would linger for days. Then he picked another spot and did it again.

Whimpers, moans, a whole cadence of sound was rolling out of Sammy now as he worked his hips in earnest against Dean. Their gasped breaths filled the heavy air and Dean released Sam's hands, sliding his own down over strong arms, muscled sides, needing to touch and be touched almost as much as he needed to release the aching pulse building at the base of his spine.

Sam's neck was going to be one big bruise by the time this was over and it only made Dean hotter, made him want to move down and mark even more skin so there wasn't an inch of Sam's body that didn't know it was his. But he couldn't give up the ecstatic friction between them, cloth and flesh working over each other, teasing and tormenting and sending them both so high they couldn't do anything but cling to one another and keep going.

Sam's jaw was sharp and smooth against his tongue and he nipped at that too, moaning as he forced his body into a furious pace, driving toward orgasm with the sear of Sam's hands pressing into his skin, branding him deep. He could feel the twitch of Sam's cock, knew he was close and yes, God, yes, that's what he wanted. He wanted to watch Sam fall over the edge, lose it all for him, cover his dick in sweet sticky need.

Dean craned his neck up, breathing rough hard breaths right into Sam's open mouth, taking his little brother's air into his lungs as it washed over his face. The flex of their hips together was punishing, both of them lost to the rhythm of blood and muscle and the siren song of white heat. Sam was keening deep in his throat, so fucking close, and Dean sank his teeth into the soft pliant flesh of his brother's lower lip hard enough to taste copper.

Sam's whole body locked up, arms like iron bands squeezing the air out of Dean's lungs and it didn't matter because he could just survive on Sam and his pleasure and the burning heat splashing between them, soaking them both in the evidence of bliss. Sam hadn't even finished pulsing out his ecstasy before Dean added his own contribution and somewhere outside of the stars flashing behind his eyelids and the throb of blood in his ears he would have sworn he heard Sam breathe 'yes'.

The pleasure left them drained, laying limply on the bed with their heads pressed together and their sweat mingling. Dean's fingers were twisted up in Sam's shaggy mane, petting through it in slow, soothing circles.

"I think you should know," Sam muttered, voice shot deep with lust and satisfaction, "I'm going to salt and burn all your boxers."

It took a minute for the laughs vibrating through their chests to make it out into the air, but once it had started, it took them a long time to stop, releasing the last of the nervous energy that lay between them. As they wound down to slow chuckles, Dean resettled his head on Sam's shoulder, half-closing his eyes.

"Fine by me Sammy," he whispered, pressing one last kiss into his brother's skin before they slipped into sleep.


End file.
